Yes, he did: both in the manga and anime.
Rather easily, in fact, in SSJ3.
he lost to buu when his fused end and buu warpped gotenks up donig there fight and he beat up gotenks he did not beat buu easliy buu was toying with gotenks he told gohan that then pwoer up when him gohan fight
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super saiyan+broly=legendary super saiyan broly--goku,s fusion+vegeta,s fusion=ssj gogeta--ss4goku,s fusion+ss4vegeta,s fusion=ssj4gogea--babidi+ssj3gotenks=gotenks buu--absorption+ultimate gohan=gohan buu--frieza,s elder brother+super transformation=cooler finaL form--frieza final form+super transformation=100% final form frieza--elder supreme kai+ssj2gohan=ultimate gohan--android17=android17=super 17--goten+trunks=gotenks
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Defense.